4-Chloroaniline → HCID 78321755, compound

HRID 1775650Notes

Reaction equation

HRID 1775650 reaction equation
[C:1]1([N:7]2[C:12](=O)C3SC=C(C4C=CC=CC=4)C=3N=C2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:23][C:24]1[C:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:35])=[CH:27][S:26][C:25]=1[C:36]([O:38]C)=O.C(OCC)(OCC)OCC.[Cl:50]C1C=CC(N)=CC=1>C(O)(=O)C>[Cl:50][C:4]1[CH:5]=[CH:6][C:1]([N:7]2[C:36](=[O:38])[C:25]3[S:26][CH:27]=[C:28]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[CH3:35])[C:24]=3[N:23]=[CH:12]2)=[CH:2][CH:3]=1

Participants

6

Reactant 4

HCID 78124-ChloroanilineHCID 31214Ethyl orthoformateHCID 783248653,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-oneHCID 86729805HCID 86729805, compound

Product 1

HCID 78321755HCID 78321755, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In the same manner as the synthesis of Compound 1, methyl 3-amino-4-(o -tolyl)thiophene-2-carboxylate (80 mg, 0.32 mmol), triethyl orthoformate (0.7 ml), 4-chloroaniline (76.8 mg, 0.6 mmol), and acetic acid (0.1 ml) were used to give 33.5 mg (0.09 mmol, 28.4% yield) of the title compound.

Sources & evidence

ORD record
ord-18e570d8605c4d6a8f6318c5acc6b8f6
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

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